126-90-9Relevant academic research and scientific papers
Monoterpene glycosides and triterpene acids from Eriobotrya deflexa
Lee,Lee,Kuo,Chou
, p. 865 - 869 (2001)
A phytochemical study on a methanolic extract of leaves of Eriobotrya deflexa led to the isolation and characterization of nine terpenoid compounds. Four of these are new chemical entities, including two monoterpene glycosides, (3S)-O-α-L-rhamnopyranosyl-(1→3)-[4-O-(E)-coumaroyl]- α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-linalool (1) and (3S)-O-α-L-rhamnopyranosyl-(1→3)-[4-O-(Z)-coumaroyl]-α-L- rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-linalool (2), and two triterpene acids, 1β,2α,19α-trihydroxy-3-oxo-12-ursen-28-oic acid (3) and 2α,3α,19α-trihydroxy-12-oleanen-28-oic acid (4). Their structures were elucidated on the basis of spectroscopic analysis. The activities of these isolates in an in vitro antiproliferation test were also determined.
1,3-Transposition of primary allylic alcohols: Synthesis of optically active secondary and tertiary allylic alcohols
Dorta, Rosa L.,Rodriguez, Maria S.,Salazar, Jose A.,Suarez, Ernesto
, p. 4675 - 4678 (1997)
The reduction of optically active 2,3-epoxy alcohols, suitably prepared by the Sharpless asymmetric epoxidation of primary allylic alcohols, with the system triphenylphosphine/ iodine/imidozole/2,6-lutidine/water, leads in a single step to optically active secondary and tertiary allylic alcohols.
Exploring castellaniella defragrans linalool (De)hydratase-isomerase for enzymatic hydration of alkenes
Engleder, Matthias,Müller, Monika,Kaluzna, Iwona,Mink, Daniel,Schürmann, Martin,Leitner, Erich,Pichler, Harald,Emmerstorfer-Augustin, Anita
, (2019/06/14)
Acyclic monoterpenes constitute a large and highly abundant class of secondary plant metabolites and are, therefore, attractive low-cost raw materials for the chemical industry. To date, numerous biocatalysts for their transformation are known, giving access to highly sought-after monoterpenoids. In view of the high selectivity associated with many of these reactions, the demand for enzymes generating commercially important target molecules is unabated. Here, linalool (de)hydratase-isomerase (Ldi, EC 4.2.1.127) from Castellaniella defragrans was examined for the regio- and stereoselective hydration of the acyclic monoterpene β-myrcene to (S)-(+)-linalool. Expression of the native enzyme in Escherichia coli allowed for identification of bottlenecks limiting enzyme activity, which were investigated by mutating selected residues implied in enzyme assembly and function. Combining these analyses with the recently published 3D structures of Ldi highlighted the precisely coordinated reduction–oxidation state of two cysteine pairs in correct oligomeric assembly and the catalytic mechanism, respectively. Subcellular targeting studies upon fusion of Ldi to different signal sequences revealed the significance of periplasmic localization of the mature enzyme in the heterologous expression host. This study provides biochemical and mechanistic insight into the hydration of β-myrcene, a nonfunctionalized terpene, and emphasizes its potential for access to scarcely available but commercially interesting tertiary alcohols.
Metal-organic framework Co(D-cam)1/2(bdc)1/2(tmdpy) for improved enantioseparations on a chiral cyclodextrin stationary phase in gas chromatography
Liu, Hong,Xie, Sheng-Ming,Ai, Ping,Zhang, Jun-Hui,Zhang, Mei,Yuan, Li-Ming
, p. 1103 - 1108 (2014/11/07)
Initial efforts to combine a chiral metal-organic framework (MOF), Co(D-Cam)1/2(bdc)1/2(tmdpy) (D-Cam=D-camphoric acid, bdc=1,4-benzenedicarboxylic acid, tmdpy=4,4′-trimethylenedipyridine), with peramylated β-cyclodextrins to investigate whether the use of a MOF can enhance enantioseparations on a cyclodextrin stationary phase are reported. Compared with columns of peramylated β-cyclodextrin incorporated in a MOF containing sodium chloride, the column of peramylated β-cyclodextrin+MOF shows excellent selectivity for the recognition of racemates, and higher resolutions are achieved on the peramylated β-cyclodextrin+MOF stationary phase. Experimental results indicate that the use of Co(D-Cam) 1/2(bdc)1/2(tmdpy) can improve enantioseparations on peramylated β-cyclodextrins. This is the first report that chiral MOFs can improve enantioseparations on a chiral stationary phase for chromatography. Copyright
Transcriptome profiling, and cloning and characterization of the main monoterpene synthases of Coriandrum sativum L.
Galata, Mariana,Sarker, Lukman S.,Mahmoud, Soheil S.
, p. 64 - 73 (2014/05/06)
Terpenoids are a large and diverse class of specialized metabolites that are essential for the growth and development of plants, and have tremendous industrial applications. The mericarps of Coriandrum sativum L. (coriander) produce an essential oil (EO) rich in monoterpenes, volatile C10 terpenoids. To investigate EO metabolism, the transcriptome of coriander mericarps, at three developmental stages (early, mid, late) was sequenced via Illumina technology and a transcript library was produced. To validate the usability of the transcriptome sequences, two terpene synthase candidate genes, CsγTRPS and CsLINS, encoding 558 and 562 amino acid proteins were expressed in bacteria, and the recombinant proteins purified by Ni-NTA affinity chromatography. The 65.16 (CsγTRPS) and 65.91 (CsLINS) kDa recombinant proteins catalyzed the conversion of geranyl diphosphate, the precursor to monoterpenes, to γ-terpinene and (S)-linalool, respectively, with apparent Vmax and Km values of 2.24 ± 0.16 (CsγTRPS); 19.63 ± 1.05 (CsLINS) pkat/mg and 66.25 ± 13 (CsγTRPS); 2.5 ± 0.6 (CsLINS) μM, respectively. Together, CsγTRPS and CsLINS account for the majority of EO constituents in coriander mericarps. Investigation of the coriander transcriptome, and knowledge gained from these experiments will facilitate future studies concerning essential and fatty acid oil production in coriander. They also enable efforts to improve the coriander oils through metabolic engineering or plant breeding.
Synthesis and reactions of the optically active selenols derived from monoterpenes Dedicated to Professor Jacek Gawronski on the occasion of his 70th birthday
Scianowski, Jacek,Rafalski, Jaroslaw,Banach, Anna,Czaplewska, Justyna,Komoszynska, Anna
, p. 1089 - 1096 (2013/10/08)
A convenient methodology for the synthesis of optically active selenols, derived from p-menthane, carane, and pinane, is described. The selenols were oxidized with air to give the optically active diselenides, and were also converted into the corresponding allylic selenides via reaction with Z- and E-cinnamyl, geranyl, and neryl chlorides. Oxidation of the allylic selenides with mCPBA gave the optically active alcohols via [2,3]-sigmatropic rearrangement of the in situ generated allylic selenoxides.
Metal-ligand core-shell nanocomposite catalysts for the selective semihydrogenation of alkynes
Mitsudome, Takato,Takahashi, Yusuke,Ichikawa, Satoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information, p. 1481 - 1485 (2013/04/10)
Catalysts with a sheltered upbringing: Novel core-shell nanocomposite catalysts consisting of active metal nanoparticles encapsulated by macroligands have been prepared. They have Pd nanoparticles (PdNPs) as an active core and shell ligands having sulfoxide moieties coordinated to the PdNPs. The shell protects the catalyst from coordination by alkenes and allows the lead-free selective semihydrogenation of a wide range of alkynes without any additives (see scheme). Copyright
Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis
Oh, Ki-Hoon,Nguyen, Giang-Son,Kim, Eun-Young,Kourist, Robert,Bornscheuer, Uwe,Oh, Tae-Kwang,Yoon, Jung-Hoon
experimental part, p. 67 - 73 (2012/09/07)
A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35°C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis.
An efficient procedure for the 1,3-transposition of allylic alcohols based on lithium naphthalenide induced reductive elimination of epoxy mesylates
Wu, Yen-Ku,Liu, Hsing-Jang,Zhu, Jia-Liang
, p. 621 - 623 (2008/12/22)
An efficient protocol for the 1,3-transposition of allylic alcohols has been developed. The method is based on the pretransformation of allylic alcohols into the corresponding epoxy mesylates, followed by the reductive elimination of the resulting epoxy mesylates by using lithium naphthalenide (LN) as a reducing agent. Georg Thieme Verlag Stuttgart.
Total partial synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3- acetoxyocta-1,7-diene and (3S, 6S)-(-)-3,7-dimethylocta-1,7-diene-3,6-diol from geraniol
Liu, Zuosheng,Lan, Jiong,Li, Yulin,Xing, Yacheng,Cen, Wen
, p. 324 - 325 (2007/10/03)
The synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3-acetoxyocta-1,7- diene and (3S, 6S)-(-)3,7-dimethylocta-1,7-diene-3,6-diol via the rearrangement of the chiral 2,3-epoxy alcohol, with the system Ph3P, pyridine, I2 and H2O, is described.
